Role of N-acetyl-N-nitroso-tryptophan as nitric oxide donor in the modulation of HIF-1-dependent signaling

Biological Chemistry

Volumn 391, Issue 5, 2010, Pages 533-540

  Berchner Pfannschmidt, Utta ^a   Tug, Suzan ^a   Hu, Jun ^a   Reyes, Buena Delos ^a   Fandrey, Joachim ^a   Kirsch, Michael ^b  

^a UNIVERSITY OF DUISBURG ESSEN   (Germany)

^b UNIVERSITY HOSPITAL ESSEN   (Germany)

Author keywords

Hypoxia inducible factor (HIF); N acetyl N nitrosotryptophan; Prolyl hydroxylase 2 (PHD2); S nitrosoglutathione (GSNO)

Indexed keywords

CARBONATE DEHYDRATASE IX; HYPOXIA INDUCIBLE FACTOR 1; MELATONIN; MESSENGER RNA; N ACETYL N NITROSO TRYPTOPHAN; N NITROSOMELATONIN; NITRIC OXIDE DONOR; PROCOLLAGEN PROLINE 2 OXOGLUTARATE 4 DIOXYGENASE; PROCOLLAGEN PROLINE 2 OXOGLUTARATE 4 DIOXYGENASE 2; S NITROSOGLUTATHIONE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; HUMAN; HUMAN CELL; HYPOXIA; PRIORITY JOURNAL; PROTEIN EXPRESSION; UPREGULATION;

CELL LINE, TUMOR; HUMANS; HYPOXIA-INDUCIBLE FACTOR 1; NITRIC OXIDE DONORS; NITROSAMINES; OSTEOSARCOMA; PROCOLLAGEN-PROLINE DIOXYGENASE; SIGNAL TRANSDUCTION; TRYPTOPHAN;

ANIMALIA;

EID: 77952805152     PISSN: 14316730     EISSN: 14374315     Source Type: Journal    
DOI: 10.1515/BC.2010.054     Document Type: Article

References (35)

1. Berchner-Pfannschmidt, U., Yamac, H., Trinidad, B., and Fandrey, J. (2007). Nitric oxide modulates oxygen sensing by hypoxiainducible factor 1-dependent induction of prolyl hydroxylase 2. J. Biol. Chem. 282, 1788-1796.
2. Berchner-Pfannschmidt, U., Tug, S., Trinidad, B., Becker, M., Oehme, F., Flamme, I., Fandrey, J., and Kirsch, M. (2008). The impact of N-nitroso-melatonin as nitric oxide donor in cell culture experiments. J. Pineal Res. 45, 489-496.
3. Berchner-Pfannschmidt, U., Tug, S., Kirsch, M., and Fandrey, J. (2010). Oxygen-sensing under the influence of nitric oxide. Cell. Signal. 22, 349-356.
4. Blanchard-Fillion, B., Servy, C., and Ducrocq, C. (2001). 1-Nitrosomelatonin is a spontaneous NO-releasing compound. Free Radic. Res. 35, 857-866.
5. Bonnett, R. and Holleyhead, R. (1974). Reaction of tryptophan derivatives with nitrite. J. Chem. Soc. Perkin Trans. 1, 962-964.
6. Czapski, G. and Goldstein, S. (1995). The role of the reactions of NO with superoxide and oxygen in biological systems: a kinetic approach. Free Radic. Biol. Med. 19, 785-794.
7. Fandrey, J., Gorr, T.A., and Gassmann, M. (2006). Regulating cellular oxygen sensing by hydroxylation. Cardiovasc. Res. 71, 642-651.
8. Herold, S., Exner, M., and Nauser, T. (2001). Kinetic and mechanistic studies of the NO-mediated oxidation of oxymyoglobin and oxyhemoglobin. Biochemistry 40, 3385-3395.
9. Herraiz, T. and Galisteo, J. (2004). Endogenous and dietary indoles: a class of antioxidants and radical scavengers in the ABTS assay. Free Radic. Res. 38, 323-331.
10. Hirsilä, M., Koivunen, P., Gunzler, V., Kivirikko, K.I., and Myllyharju, J. (2003). Characterization of the human prolyl 4-hydroxylases that modify the hypoxia-inducible factor. J. Biol. Chem. 278, 30772-30780.
11. Holmes, A.J. and Williams, D.L.H. (2000). Reaction of ascorbic acid with S-nitrosothiols: clear evidence for two distinct reaction pathways. J. Chem. Soc. Perkin Trans. 2, 1639-1644.
12. Ignarro, L.J. (1990). Biosynthesis and metabolism of endotheliumderived nitric oxide. Annu. Rev. Pharmacol. Toxicol. 30, 535-560.
13. Kageyama, Y., Koshiji, M., To, K.K., Tian, Y.M., Ratcliffe, P.J., and Huang, L.E. (2004). Leu-574 of human HIF-1a is a molecular determinant of prolyl hydroxylation. FASEB J. 18, 1028-1030.
14. Kirsch, M. and de Groot, H. (2005). First insights into regiospecific transnitrosation reactions between tryptophan derivatives: melatonin as an effective target. J. Pineal Res. 38, 247-253.
15. Kirsch, M. and Korth, H.-G. (2007). Generation, basic chemistry, and detection of N-nitrosotryptophan derivatives. Org. Biomol. Chem. 5, 3889-3894.
16. Kirsch, M. and de Groot, H. (2008). N-Nitrosomelatonin outcompensates S-nitrosocysteine in inhibiting glyceraldehyde 3-phosphate dehydrogenase: first evidence that N-nitrosomelatonin can modify protein function. J. Pineal Res. 44, 244-249.
17. Kirsch, M., Korth, H.-G., Sustmann, R., and de Groot, H. (2002). The pathobiochemistry of nitrogen dioxide. Biol. Chem. 383, 389-399.
18. Kirsch, M., Fuchs, A., and de Groot, H. (2003). Regiospecific nitrosation of N-(terminal) blocked tryptophan derivatives by N2O3 at physiological pH. J. Biol. Chem. 278, 11931-11936.
19. Kopczak, A., Korth, H.-G., de Groot, H., and Kirsch, M. (2007). NNitroso-melatonin releases nitric oxide in the presence of serotonin and its derivatives. J. Pineal Res. 43, 343-350.
20. Kytzia, A., Korth, H.-G., de Groot, H., and Kirsch, M. (2006a). Catecholamine-induced release of nitric oxide from N-nitrosotryptophan derivatives: a non-enzymatic way of catecholamineoxidation. Org. Biomol. Chem. 4, 257-267.
21. Kytzia, A., Korth, H.-G., Sustmann, R., de Groot, H., and Kirsch, M. (2006b). On the mechanism of the ascorbic acid-induced release of nitric oxide from nitrosated tryptophan derivatives. Scavenging of NO by ascorbyl radicals. Chem. Eur. J. 12, 8786-8797.
22. Lehnig, M. and Kirsch, M. (2007). 15N-CIDNP investigations during tryptophan, N-acetyl-L-tryptophan, and melatonin nitration with reactive nitrogen species. Free Radic. Res. 41, 523-535.
23. Lipton, A.J., Johnson, M.A., Macdonald, T., Lieberman, M.W., Gozal, D., and Gaston, B. (2001). S-Nitrosothiols signal the ventilatory response to hypoxia. Nature 413, 171-174.
24. Metzen, E., Zhou, J., Jelkmann, W., Fandrey, J., and Brune, B. (2003). Nitric oxide impairs normoxic degradation of HIF-1a by inhibition of prolyl hydroxylases. Mol. Biol. Cell 14, 3470-3481.
25. Moncada, S., Palmer, R.M.J., and Higgs, E.A. (1991). Nitric oxide: physiology, pathophysiology, and pharmacology. Pharmacol. Rev. 43, 109-142.
26. Müller, C., Korth, H.-G., de Groot, H., and Kirsch, M. (2007). Reaction of vitamin E compounds with N-nitrosated tryptophan derivatives and its analytical use. Chem. Eur. J. 13, 7532-7542.
27. Oehme, F., Jonghaus, W., Narouz-Ott, L., Huetter, J., and Flamme, I. (2004). A nonradioactive 96-well plate assay for the detection of hypoxia-inducible factor prolyl hydroxylase activity. Anal. Biochem. 330, 74-80.
28. Pastorek, J., Pastorekova, S., Callebaut, I., Mornon, J., Zelnik, V., Opavsky, R., Zatovicova, M., Liao, S., Portetele, D., Stanbridge, E., et al. (1994). Cloning and characterization of MN, a human tumor-associated protein with a domain homologous to carbonic anhydrase and a putative helix-loop-helix DNA binding segment. Oncogene 9, 2877-2888.
29. Pawloski, J.R., Hess, D.T., and Stamler, J.S. (2001). Export by red blood cells of nitric oxide bioactivity. Nature 409, 622-626.
30. Rose, W.C., Coon, M.J., Lambert, G.F., and Howe, E.E. (1955). The amino acid requirements of man. VIII. The metabolic availability of the optical isomers of acetyltryptophan. J. Biol. Chem. 212, 201-205.
31. Smith, J.N. and Dasgupta, T.P. (2000). Kinetics and mechanism of the decomposition of S-nitrosoglutathione by L-ascorbic acid and copper ions in aqueous solution to produce nitric oxide. Nitric Oxide 4, 57-66.
32. Sonnenschein, K., de Groot, H., and Kirsch, M. (2004). Formation of S-nitrosothiols from regiospecific reaction of thiols with Nnitrosotryptophan- derivatives. J. Biol. Chem. 279, 45433-45440.
33. Stamler, J.S., Lamas, S., and Fang, F.C. (2001). Nitrosylation: the prototypic redox-based signaling mechanism. Cell 106, 675-683.
34. Taha, Z., Kiechle, F., and Malinski, T. (1992). Oxidation of nitric oxide by oxygen in biological systems monitored by porphyrinic sensor. Biochem. Biophys. Res. Commun. 188, 734-739.
35. Turjanski, A.G., Leonik, F., Estrin, D.A., Rosenstein, R.E., and Doctorovich, F. (2000). Scavenging of NO by melatonin. J. Am. Chem. Soc. 122, 10468-10469.